20,084

Dukes, MA Homes

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  • 19 Old Woods Rd, Chilmark, MA 02535
    19 Old Woods Rd, Chilmark, MA 02535
    19 Old Woods Rd, Chilmark, MA 02535
    /41

    $2,950,000

    • 4 Beds
    • 3 Baths
    • 2,424 Sq Ft

    19 Old Woods Rd, Chilmark, MA 02535

    Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his

    Cheri Mason Landvest MV

    19 Old Woods Rd, Chilmark, MA 02535
  • 223 Sandpiper Lane Vh405, Tisbury, MA 02568
    223 Sandpiper Lane Vh405, Tisbury, MA 02568
    223 Sandpiper Lane Vh405, Tisbury, MA 02568
    /17

    $12,000 per month

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • House for Rent

    223 Sandpiper Lane Vh405, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

    Karen Overtoom Karen M. Overtoom R.E.

    223 Sandpiper Lane Vh405, Tisbury, MA 02568
  • 25 Simpson's Ln, Edgartown, MA 02539
    25 Simpson's Ln, Edgartown, MA 02539
    25 Simpson's Ln, Edgartown, MA 02539
    /18

    $3,350,000 Sold Jun 05, 2025

    • 3,156 Sq Ft
    • $1061/SF
    • 138 Days On Market
    • 6 Beds
    • 6 Baths
    • Built 1900

    25 Simpson's Ln, Edgartown, MA 02539

    Nestled in the heart of Edgartown, is this historic residence known as The Lightkeeper’s Inn. This property has five bedrooms, five baths and a separate one bedroom, one bath cottage, on .20 acre. Beautifully decorated in ole Vineyard style, the residence has the island feel of old time Martha’s Vineyard. This 5BD/5BA home sits in the heart of Edgartown close to the waterfront. Known as The

    Greg Hartel Hartel Realty

    25 Simpson's Ln, Edgartown, MA 02539
    • 26 Chappaquiddick Ave, Vineyard Haven, MA 02568
      26 Chappaquiddick Ave, Vineyard Haven, MA 02568
      26 Chappaquiddick Ave, Vineyard Haven, MA 02568
      /16

      Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,275 Sq Ft

      26 Chappaquiddick Ave, Vineyard Haven, MA 02568

      26 Chappaquiddick Ave, Vineyard Haven, MA 02568
  • 11 By the Woods, Chilmark, MA 02535
    11 By the Woods, Chilmark, MA 02535
    11 By the Woods, Chilmark, MA 02535
    /35

    $2,850,000

    • 4 Beds
    • 3 Baths
    • 2,967 Sq Ft

    11 By the Woods, Chilmark, MA 02535

    Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main House,

    Julianna Flanders Flanders Real Estate

    11 By the Woods, Chilmark, MA 02535
  • 100 Connie's Way Vh401, Tisbury, MA 02568
    100 Connie's Way Vh401, Tisbury, MA 02568
    100 Connie's Way Vh401, Tisbury, MA 02568
    /34

    $25,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,334 Sq Ft
    • House for Rent

    100 Connie's Way Vh401, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

    Karen Overtoom Karen M. Overtoom R.E.

    100 Connie's Way Vh401, Tisbury, MA 02568
  • 5 Vincent Rd, Vineyard Haven, MA 02568
    5 Vincent Rd, Vineyard Haven, MA 02568
    5 Vincent Rd, Vineyard Haven, MA 02568
    /3

    $1,695,000 Sold May 30, 2025

    • 1,296 Sq Ft
    • $1308/SF
    • 2 Beds
    • 2 Baths
    • Built 1960

    5 Vincent Rd, Vineyard Haven, MA 02568

    NOT LISTED IN LINK

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    5 Vincent Rd, Vineyard Haven, MA 02568
    • 1 Gray Gull Cir, Edgartown, MA 02539
      1 Gray Gull Cir, Edgartown, MA 02539
      1 Gray Gull Cir, Edgartown, MA 02539
      /27

      Est $2,157,469 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,428 Sq Ft

      1 Gray Gull Cir, Edgartown, MA 02539

      1 Gray Gull Cir, Edgartown, MA 02539
  • 16 Atlantic Ave, Oak Bluffs, MA 02557
    16 Atlantic Ave, Oak Bluffs, MA 02557
    16 Atlantic Ave, Oak Bluffs, MA 02557
    /39

    $2,495,000

    • 5 Beds
    • 2.5 Baths
    • 2,577 Sq Ft

    16 Atlantic Ave, Oak Bluffs, MA 02557

    East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most

    Katherine Donahue Sandpiper Realty Inc

    16 Atlantic Ave, Oak Bluffs, MA 02557
  • 6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    /26

    $50,700 per month

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft
    • House for Rent

    6 Trails End Ch241, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

    Karen Overtoom Karen M. Overtoom R.E.

    6 Trails End Ch241, Chilmark, MA 02535
  • 14 Galway Rd, Vineyard Haven, MA 02568
    14 Galway Rd, Vineyard Haven, MA 02568
    14 Galway Rd, Vineyard Haven, MA 02568
    /15

    $1,150,000 Sold May 30, 2025

    • 1,338 Sq Ft
    • $859/SF
    • 48 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1966

    14 Galway Rd, Vineyard Haven, MA 02568

    Welcome to 14 Galway Road, West Tisbury. The home and property have been lovingly maintained and used by the same family since the home was built. It offers an open eat-in kitchen/living room design with a masonry fireplace. On the first floor are two bedrooms, one full bathroom, a linen closet, and hidden washer and dryer along the hallway. The stairway brings you to a second floor which

    Michele Casavant Vineyard Village Realty

    14 Galway Rd, Vineyard Haven, MA 02568
    • 7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      /31

      Est $2,432,400 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,386 Sq Ft

      7 the Aerie, Chilmark, MA 02535

      7 the Aerie, Chilmark, MA 02535
  • 18 Allen Farm Rd, Chilmark, MA 02535
    18 Allen Farm Rd, Chilmark, MA 02535
    18 Allen Farm Rd, Chilmark, MA 02535
    /13

    $2,950,000

    • 1 Bed
    • 1 Bath
    • 726 Sq Ft

    18 Allen Farm Rd, Chilmark, MA 02535

    Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1 + bedroom cottage with screened porch, brick patio and outside shower. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered fully furnished,

    Patty Kendall Kendall & Kendall

    18 Allen Farm Rd, Chilmark, MA 02535
  • 17 Round Pond Rd Ch240, Chilmark, MA 02535
    17 Round Pond Rd Ch240, Chilmark, MA 02535
    17 Round Pond Rd Ch240, Chilmark, MA 02535
    /39

    $110,000 per month

    • 5 Beds
    • 5 Baths
    • 4,000 Sq Ft
    • House for Rent

    17 Round Pond Rd Ch240, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Round Pond Rd Ch240, Chilmark, MA 02535
  • 10 Rumpus Ridge Rd, Chilmark, MA 02535
    10 Rumpus Ridge Rd, Chilmark, MA 02535
    10 Rumpus Ridge Rd, Chilmark, MA 02535
    /32

    $1,050,000 Sold May 29, 2025

    • 1,701 Sq Ft
    • $617/SF
    • 28 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1960

    10 Rumpus Ridge Rd, Chilmark, MA 02535

    Discover this inviting two-unit property in the heart of Chilmark! Ideally situated near Chilmark General Store, Squibnocket, Menemsha, and the pristine shores of Lucy Vincent Beach, this home offers both convenience and charm. Thoughtfully updated for year-round comfort, the property features a new metal roof, new siding, solar panels, mini-split AC, and more. The main-level residence offers

    Peyton Wallace Studio Realty

    10 Rumpus Ridge Rd, Chilmark, MA 02535
    • 5 Bold Meadow Cir, Edgartown, MA 02539
      5 Bold Meadow Cir, Edgartown, MA 02539
      5 Bold Meadow Cir, Edgartown, MA 02539
      /23

      Est $2,907,034 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,252 Sq Ft

      5 Bold Meadow Cir, Edgartown, MA 02539

      5 Bold Meadow Cir, Edgartown, MA 02539
  • 111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    /44

    $2,748,000

    • 6 Beds
    • 4 Baths
    • 2,400 Sq Ft

    111 Eastville Ave, Oak Bluffs, MA 02557

    JUST REDUCED!! Steps to the beach- Minutes to downtown Oak Bluffs and Vineyard Haven. This is a perfect location.FULLY FURNISHED, TURNKEY, with an impressive rental history. Situated on an oversized lot that is two parcels away from the beach. This home offers six bedrooms and four

    Ed Charter Arrowhead Homes

    111 Eastville Ave, Oak Bluffs, MA 02557
  • 44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    /19

    $24,000 per month

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    44 Flanders Ln, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

    Karen Overtoom Karen M. Overtoom R.E.

    44 Flanders Ln, Chilmark, MA 02535
  • 9 Hollow Way, Edgartown, MA 02539
    9 Hollow Way, Edgartown, MA 02539
    9 Hollow Way, Edgartown, MA 02539
    /74

    $3,284,500 Sold May 23, 2025

    • 3,085 Sq Ft
    • $1065/SF
    • 657 Days On Market
    • 6 Beds
    • 6 Baths
    • Built 2024

    9 Hollow Way, Edgartown, MA 02539

    EDGARTOWN - NEW CONSTRUCTION with POOL - 6 Bedrooms...in Two Structures.....Plus a 31'6" x 14' heated saltwater pool! 5 Bedroom Main House with 4.5 Bathrooms. Detached 1 bedroom w/Full Bathroom over a Two (2) car garage. Main house has a lovely open floor plan with a large kitchen w/Bosch Stainless Steel Appliances, beautiful Soapstone Island and Carrara Marble counters, a dining room,

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    9 Hollow Way, Edgartown, MA 02539
    • 23 Majors Cove Ln, Edgartown, MA 02539
      23 Majors Cove Ln, Edgartown, MA 02539
      23 Majors Cove Ln, Edgartown, MA 02539
      /22

      Est $2,812,863 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,050 Sq Ft

      23 Majors Cove Ln, Edgartown, MA 02539

      23 Majors Cove Ln, Edgartown, MA 02539
  • 10 Wood Duck Way, Oak Bluffs, MA 02557
    10 Wood Duck Way, Oak Bluffs, MA 02557
    10 Wood Duck Way, Oak Bluffs, MA 02557
    /42

    $2,500,000

    • 4 Beds
    • 3.5 Baths
    • 1 Sq Ft

    10 Wood Duck Way, Oak Bluffs, MA 02557

    Perched on a hill, this waterfront house encompasses three levels of living. Thoughtfully designed and well cared for, this home provides calming water views and direct access to Wiggy's freshwater Pond from almost every room. The main level boasts a kitchen fitted with high-end appliances and opens to the dining room, deck, and airy living room with exposed beams, a gas fireplace, and large

    Marcia Sullivan Garvey Donnelly + Co.

    10 Wood Duck Way, Oak Bluffs, MA 02557
  • 384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    /31

    $40,000 per month

    • 6 Beds
    • 6 Baths
    • 3,960 Sq Ft
    • House for Rent

    384 Middle Rd Ch222, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

    Karen Overtoom Karen M. Overtoom R.E.

    384 Middle Rd Ch222, Chilmark, MA 02535
  • 41 Smith Hollow Dr, Edgartown, MA 02539
    41 Smith Hollow Dr, Edgartown, MA 02539
    41 Smith Hollow Dr, Edgartown, MA 02539
    /37

    $1,835,000 Sold May 23, 2025

    • 2,391 Sq Ft
    • $767/SF
    • 59 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2001

    41 Smith Hollow Dr, Edgartown, MA 02539

    Discover this exquisite, contemporary home nestled in the heart of Edgartown's Smith Hollow, conveniently located just off the bike path and mere minutes from the lively Edgartown Village. Situated in a welcoming, family-oriented neighborhood, this stylish residence boasts a bright and airy open floor plan.The Great Room captivates with its soaring cathedral wood ceiling and robust timber accent

    Marilyn Moses Ocean Park Realty Inc

    41 Smith Hollow Dr, Edgartown, MA 02539
    • 225 Bigelow Rd, Vineyard Haven, MA 02568
      225 Bigelow Rd, Vineyard Haven, MA 02568
      225 Bigelow Rd, Vineyard Haven, MA 02568
      /32

      Est $4,888,183 Not Listed For Sale

      • 5 Beds
      • 8 Baths
      • 5,305 Sq Ft

      225 Bigelow Rd, Vineyard Haven, MA 02568

      225 Bigelow Rd, Vineyard Haven, MA 02568
  • 79 David Ave, Vineyard Haven, MA 02568
    79 David Ave, Vineyard Haven, MA 02568
    79 David Ave, Vineyard Haven, MA 02568
    /37

    $2,725,000

    • 5 Beds
    • 4.5 Baths
    • 4,982 Sq Ft

    79 David Ave, Vineyard Haven, MA 02568

    BEAUTIFUL CUSTOM-BUILT RETREAT- LAMBERT'S COVE This impressive property offers the perfect blend of privacy and convenient access to downtown and the picturesque James Pond Reserve at Lambert's Cove Beach. Step inside to discover over 4,900 sq ft of recently renovated living space. The home boasts 5 bedrooms and 4.5 bathrooms, including a stunning chef's kitchen that will ignite your culinary

    Tina Miller Compass

    79 David Ave, Vineyard Haven, MA 02568
  • 19 Lake Rd, Chilmark, MA 02535
    19 Lake Rd, Chilmark, MA 02535
    19 Lake Rd, Chilmark, MA 02535
    /32

    $42,000 per month

    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    19 Lake Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lake Rd, Chilmark, MA 02535
  • 8 Massasoit Rd, Edgartown, MA 02539
    8 Massasoit Rd, Edgartown, MA 02539
    8 Massasoit Rd, Edgartown, MA 02539
    /33

    $1,790,000 Sold May 23, 2025

    • 1,674 Sq Ft
    • $1069/SF
    • 36 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1977

    8 Massasoit Rd, Edgartown, MA 02539

    This incredibly charming Katama Cape Cod-style home that has been completely refreshed top to bottom! An updated kitchen with high-end appliances, including a wine fridge, two brand new bathrooms, central AC, new heating system, and a new second floor deck are just some of the improvements. There are two bedrooms, one on each floor. The second floor has a comfortable lounge area, and a cozy loft

    Cheri Mason Landvest MV

    8 Massasoit Rd, Edgartown, MA 02539
    • 3 Duarte Cir, Edgartown, MA 02539
      3 Duarte Cir, Edgartown, MA 02539
      3 Duarte Cir, Edgartown, MA 02539
      /7

      Est $4,090,508 Not Listed For Sale

      • 6 Beds
      • 7 Baths
      • 6,783 Sq Ft

      3 Duarte Cir, Edgartown, MA 02539

      3 Duarte Cir, Edgartown, MA 02539
  • 6 Church St, Aquinnah, MA 02535
    6 Church St, Aquinnah, MA 02535
    6 Church St, Aquinnah, MA 02535
    /33

    $2,395,000

    • 3 Beds
    • 3 Baths
    • 1,862 Sq Ft

    6 Church St, Aquinnah, MA 02535

    This beautifully renovated contemporary home is perched on a hillside, offering views of the Atlantic Ocean. Upon entering the home has a light and airy atmosphere with cathedral ceilings and a wall of windows connecting you with the outdoors. The main level consists of an open-concept kitchen, living, and dining area with soaring ceilings and sliding glass doors that overlook the treetops of

    Heidi Vanderhoop Tea Lane Associates

    6 Church St, Aquinnah, MA 02535
  • 31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    /20

    $16,800 per month

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    31 S Ridge Rd Ch218, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

    Karen Overtoom Karen M. Overtoom R.E.

    31 S Ridge Rd Ch218, Chilmark, MA 02535
  • 60 Prospect Ave, Oak Bluffs, MA 02557
    60 Prospect Ave, Oak Bluffs, MA 02557
    60 Prospect Ave, Oak Bluffs, MA 02557
    /28

    $1,270,000 Sold May 23, 2025

    • 2,192 Sq Ft
    • $579/SF
    • 57 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1940

    60 Prospect Ave, Oak Bluffs, MA 02557

    OAK BLUFFS ~ APPROVED 4 BEDROOM SEPTIC IN PLACE - This home LIVES LARGE and offers 3 Distinct Structures situated on a BEAUTIFUL landscaped .34 Acre private lot ~EASY WALK or BIKE RIDE to OAK BLUFFS HARBOR, Town, Sandy Beaches, Ferry Ports and Town Parks! Tastefully renovated SPACIOUS Split-Level Home featuring a lovely and functional open floor plan. The main level displays beautiful hardwood

    Marilyn Moses Ocean Park Realty Inc

    60 Prospect Ave, Oak Bluffs, MA 02557
    • 10 Codman Spring Rd, Edgartown, MA 02539
      10 Codman Spring Rd, Edgartown, MA 02539
      10 Codman Spring Rd, Edgartown, MA 02539
      /32

      Est $2,915,965 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,101 Sq Ft

      10 Codman Spring Rd, Edgartown, MA 02539

      10 Codman Spring Rd, Edgartown, MA 02539
  • 26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
    /13

    $2,650,000

    • 4 Beds
    • 3 Baths
    • 2,299 Sq Ft

    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

    Discover the rare opportunity to build your dream home in one of the island’s most sought-after locations off Lamberts Cove Road. This parcel offers year-round waterfront living with the ultimate blend of privacy, beach access, and design potential, without the usual coastal erosion concerns. Approved architectural plans by Moskow Linn Architects are in place for a four-bedroom main residence, a

    Jill Napior Tea Lane Associates

    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
  • 29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    /32

    $36,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    29 Cemetery Rd Ch216, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

    Karen Overtoom Karen M. Overtoom R.E.

    29 Cemetery Rd Ch216, Chilmark, MA 02535
  • 51 Rural Cir, Oak Bluffs, MA 02557
    51 Rural Cir, Oak Bluffs, MA 02557
    51 Rural Cir, Oak Bluffs, MA 02557
    /24

    $665,000 Sold May 23, 2025

    • 806 Sq Ft
    • $825/SF
    • 171 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1876

    51 Rural Cir, Oak Bluffs, MA 02557

    The Spirit of '76 is a lovely Campground cottage nestled into the landscape for privacy and shade. Just a couple of blocks to the beach, town center, shops, and restaurants. A fabulous wrap around porch with various seating areas. Built in 1876 this wonderful throwback of yesteryear features some original furnishings included in the sale. With a classic front parlor, dining room, and kitchen, a

    Lisa Lucier Anchor Realty of Martha's Vineyard

    51 Rural Cir, Oak Bluffs, MA 02557
    • 46 Windsor Dr, Edgartown, MA 02539
      46 Windsor Dr, Edgartown, MA 02539
      46 Windsor Dr, Edgartown, MA 02539
      /19

      Est $1,353,179 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft

      46 Windsor Dr, Edgartown, MA 02539

      46 Windsor Dr, Edgartown, MA 02539
  • 400 Barnes Rd, Vineyard Haven, MA 02568
    400 Barnes Rd, Vineyard Haven, MA 02568
    400 Barnes Rd, Vineyard Haven, MA 02568
    /43

    $6,395,000

    • 6 Beds
    • 6 Baths
    • 7,000 Sq Ft

    400 Barnes Rd, Vineyard Haven, MA 02568

    Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

    Jennifer DaSilva Compass | Point B

    400 Barnes Rd, Vineyard Haven, MA 02568
  • 2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    /33

    $22,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • 2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557
    2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557
    2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557
    /27

    $1,600,000 Sold May 22, 2025

    • 1,594 Sq Ft
    • $1004/SF
    • 532 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1933

    2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

    Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the

    Carol Shore Donnelly + Co

    2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557
    • 125 Skiff Ave, Vineyard Haven, MA 02568
      125 Skiff Ave, Vineyard Haven, MA 02568
      125 Skiff Ave, Vineyard Haven, MA 02568
      /34

      Est $1,384,678 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,640 Sq Ft

      125 Skiff Ave, Vineyard Haven, MA 02568

      125 Skiff Ave, Vineyard Haven, MA 02568

Showing Results 161 - 200, Page 5 of 18

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